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Identification
NameThenoyltrifluoroacetone
Accession NumberDB04795
TypeSmall Molecule
GroupsExperimental
Description

Thenoyltrifluoroacetone is a chelating agent and inhibitor of cellular respiration. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
.alpha.-ThenoyltrifluoroacetoneNot AvailableNot Available
1-Thenoyl-3,3,3-trifluoroacetoneNot AvailableNot Available
1,1,1-Trifluoro-3-(2-thenoyl)acetoneNot AvailableNot Available
2-ThenoyltrifluoroacetoneNot AvailableNot Available
alpha-ThenoyltrifluoroacetoneNot AvailableNot Available
Perfluoroacetyl(2-thenoyl)methaneNot AvailableNot Available
TTFANot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number326-91-0
WeightAverage: 222.184
Monoisotopic: 221.996234709
Chemical FormulaC8H5F3O2S
InChI KeyTXBBUSUXYMIVOS-UHFFFAOYSA-N
InChI
InChI=1S/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2
IUPAC Name
4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione
SMILES
FC(F)(F)C(=O)CC(=O)C1=CC=CS1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassKetones
Direct ParentAryl alkyl ketones
Alternative Parents
Substituents
  • Aryl alkyl ketone
  • 1,3-diketone
  • 1,3-dicarbonyl compound
  • Heteroaromatic compound
  • Thiophene
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organofluoride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsStudies indicate that thenoyltrifluoroacetone is a potent inhibitor of carboxylesterase activity, in addition to its ability to inhibit mitochondrial complex II activity.
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9964
Caco-2 permeable+0.537
P-glycoprotein substrateNon-substrate0.8104
P-glycoprotein inhibitor INon-inhibitor0.7748
P-glycoprotein inhibitor IINon-inhibitor0.783
Renal organic cation transporterNon-inhibitor0.8788
CYP450 2C9 substrateNon-substrate0.8094
CYP450 2D6 substrateNon-substrate0.8448
CYP450 3A4 substrateNon-substrate0.7506
CYP450 1A2 substrateNon-inhibitor0.6133
CYP450 2C9 substrateInhibitor0.582
CYP450 2D6 substrateNon-inhibitor0.7097
CYP450 2C19 substrateInhibitor0.7893
CYP450 3A4 substrateNon-inhibitor0.7544
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5302
Ames testNon AMES toxic0.5586
CarcinogenicityNon-carcinogens0.6418
BiodegradationNot ready biodegradable0.8573
Rat acute toxicity2.7650 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9736
hERG inhibition (predictor II)Non-inhibitor0.9203
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point42 °CPhysProp
boiling point96-98 °C at 8.00E+00 mm HgPhysProp
logP1.46HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0752 mg/mLALOGPS
logP2.37ALOGPS
logP2.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.17ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.26 m3·mol-1ChemAxon
Polarizability16.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.36 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Zhang JG, Fariss MW: Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. Biochem Pharmacol. 2002 Feb 15;63(4):751-4. Pubmed
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Liver carboxylesterase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Liver carboxylesterase 1 P23141 Details

References:

  1. Zhang JG, Fariss MW: Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. Biochem Pharmacol. 2002 Feb 15;63(4):751-4. Pubmed
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial P31040 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

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Drug created on September 11, 2007 11:49 / Updated on September 16, 2013 17:25